Sodium Hydroxide → 4-((2-Hydroxyethyl)thio)phenol

To a solution of 10.9 g 4-hydroxythiophenol (87 mmol) in 200 ml MeOH was added at 0-5° C. 87 ml 1N NaOH (87 mmol). After the reaction mixture was stirred for 10 min 6.1 ml bromoethanol (86 mmol) dissolved in 100 ml MeOH was added. The reaction mixture was stirred for 3 h at r.t. and the methanol was partly removed under reduced pressure. The residue was poured to a 1:1 mixture of ethyl acetate and saturated NaHCO3−solution and the organic phase was separated, dried over MgSO4, filtrated and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel (ethyl acetate/hexane 3/2 to 2/1) to give 13.4 g product (78.7 mmol, 91%) as a white solid.

1. additionwas added
2. customthe methanol was partly removed under reduced pressure
3. additionThe residue was poured to a 1:1 mixture of ethyl acetate and saturated NaHCO3−solution
4. customthe organic phase was separated
5. dry with materialdried over MgSO4
6. filtrationfiltrated
7. customthe solvent was removed under reduced pressure
8. customThe residue was purified by chromatography over silica gel (ethyl acetate/hexane 3/2 to 2/1)

ORD record

ord-c51708b3b9044e618611db9e9e005721

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310213B1